diff --git a/src/main/java/org/jruby/ext/openssl/PKey.java b/src/main/java/org/jruby/ext/openssl/PKey.java
index ef612eb1..417ec087 100644
--- a/src/main/java/org/jruby/ext/openssl/PKey.java
+++ b/src/main/java/org/jruby/ext/openssl/PKey.java
@@ -147,6 +147,14 @@ public static IRubyObject read(final ThreadContext context, IRubyObject recv, IR
                     debugStackTrace(runtime, "PKey readPrivateKeyFromDER", e); /* ignore */
                 }
             }
+            // d2i_PrivateKey_bio - PKCS#1 RSA, DSA and SEC1 EC keys (as written by #to_der)
+            if (keyPair == null) {
+                try {
+                    keyPair = org.jruby.ext.openssl.impl.PKey.readPrivateKeyDER(str.getBytes());
+                } catch (IOException e) {
+                    debugStackTrace(runtime, "PKey readPrivateKeyDER", e); /* ignore */
+                }
+            }
             // PEM_read_bio_PrivateKey
             if (keyPair != null) {
                 final String alg = getAlgorithm(keyPair);
diff --git a/src/main/java/org/jruby/ext/openssl/impl/PKey.java b/src/main/java/org/jruby/ext/openssl/impl/PKey.java
index 25d28faa..92859244 100644
--- a/src/main/java/org/jruby/ext/openssl/impl/PKey.java
+++ b/src/main/java/org/jruby/ext/openssl/impl/PKey.java
@@ -209,6 +209,20 @@ public static KeyPair readRSAPrivateKey(final KeyFactory rsaFactory, final byte[
         return null;
     }
 
+    // d2i_PrivateKey_bio - type specific DER encodings (PKCS#1 RSA, DSA, SEC1 EC)
+    public static KeyPair readPrivateKeyDER(final byte[] input) throws IOException {
+        try {
+            // each reader matches on sequence shape so order does not matter
+            KeyPair keyPair = readRSAPrivateKey(input);
+            if (keyPair == null) keyPair = readDSAPrivateKey(input);
+            if (keyPair == null) keyPair = readECPrivateKey(input);
+            return keyPair;
+        }
+        catch (Exception e) { // the EC reader mocks up a PrivateKeyInfo and blows up in all sorts of ways
+            throw new IOException("Could not parse private key: " + e.getMessage(), e);
+        }
+    }
+
     // d2i_RSAPublicKey_bio
     public static PublicKey readRSAPublicKey(final byte[] input)
         throws IOException, NoSuchAlgorithmException, InvalidKeySpecException {
diff --git a/src/test/ruby/test_pkey.rb b/src/test/ruby/test_pkey.rb
index 10b831f1..a7d5d6ad 100644
--- a/src/test/ruby/test_pkey.rb
+++ b/src/test/ruby/test_pkey.rb
@@ -67,6 +67,16 @@ def test_pkey_read_pkcs8_and_check_with_cert
     assert_true cert.check_private_key(pkey)
   end
 
+  # #to_der writes PKCS#1 (RSA, DSA) or SEC1 (EC), PKey.read only handled PKCS#8
+  def test_pkey_read_der_round_trip
+    %w[rsa2048 dsa2048 p256].each do |name|
+      key = Fixtures.pkey(name)
+      read = OpenSSL::PKey.read(key.to_der)
+      assert_instance_of key.class, read
+      assert_equal key.to_der, read.to_der
+    end
+  end
+
   def test_pkey_pem_file_error
     begin
       ret = OpenSSL::PKey.read('not a PEM file')